Taste of Regret
by whennext2you
Summary: Dean was invited to a party, Sam wears a diguise, things go wrong.. Teen!Chester. Dean/Sam Wincest


**Title: **Taste of Regrets

**Rate:** T (just to be safe, nothing too bad)

**Couple:** Teen!Chester. Dean/Sam. Wincest

**Disclaimer:** I don't own Dean and Sam Winchester. I do own the plot

**Summary:** Dean was invited to a party, Sam wear's a diguise, things go wrong..

* * *

When Sam was 16 his height shot up and he was taller than Dean easily. He was 6'3" overnight from his past 5'5½" height when he was 15. Dean was stuck at 5'11" so this plan would've only worked when said Sam was 15.

At 15, Dean was 19; he also was a hunter undercover most of the time. When Sam was 12 he broke his leg from a hunt and had to lie to his teacher that he fell down a flight of stairs when he actually was pushed down two flights of stairs by a poltergeist that was after his father.

At 19, Dean was the big man around the bars and parties. Everyone was in love with him or was just completely jealous and wanted to be him. One night though, the party called for "Must have a date" that's where the problems happened. His father made him swear that he'd never get into a car with a girl to make sure that they weren't possessed and trying to kill him, John had that experience before and has been on edge ever since.

So…Dean had to make the decision of meeting the girl at the party who was usually 21 or older, or use Option B. Option B was interesting and in the end he rejected all the girls and told then that he'd see them at the party. He had his Option B.

"Sammy," Dean sing-songed to his younger and shorter brother who was thin with long hairless legs.

"What Dean," Sam answered back with his high voice, it was soon going to be deep, but he had a few months left before that would happened.

"I was wondering if you'd like to hang out tonight, first we'd go to a party and then we'd hang out." Sam looked at his brother looking for a hint of doubt or something that must've been in for Dean.

"Did Dad put you up to this?"

"Now that you mention it I have to run this by Dad to make sure that he would say yes to all of this tom-foolery."

"All of this what?" Sam was definitely confused.

"Tom-foolery," he batted his eyelashes.

"Alright, who are you and where's Dean?" Alright **Step One: Make Sam all flustered and confused. **_**Complete.**_

"I'll take that as a yes," Dean grabbed his brother's arm and pulled him to the den of the motel where their Dad was taking a nap on the sofa.

**Step Two: Persuade Dad to say yes. Use lying if needed. Don't be too desperate.**

"Hey, Dad," Dean called and shook his father awake. "Sam really wanted to see this new movie that came out yesterday; can we go see it tonight?"

"Oh, you mean the one with the monsters," John Winchester pondered.

"Yes, sir," Dean nodded; he had done some research beforehand to make sure he got his facts straight. Sam was still computing the whole conversation they had earlier.

"Alright, I don't want you boys out too late, be back by 1 tonight."

"Alright," Dean smiled. He made sure that the movie he had picked out a movie that intrigued his father so he wouldn't give him a lecture on how mind rotting and a waste of money it would've been to see that movie. So **Step Two. **_**Complete.**_

Dean saw that time was running out, John had called to them that he was going to a bar for a little while. That was great timing. The party was at 8, it was 6:30 already. The party was at one of his friend's house and really none of them had seen his brother before so it was good.

"Okay, Sam. You may hate me for this, but I'm going to need you to wear a dress…"

"A what," Sam asked confused.

"A dress and some heels. You will have to be a girl. You are my date to this party."

"A what…?"

"Quick acting so surprised," Dean hit his arm and Sam became more reluctant.

"Fine, then good luck getting me into a dress," Sam cackled and got up and raced into the bathroom and locked himself in.

"You are so difficult," Dean sighed and walked over to the door after grabbing a hanger, breaking it and then using it as a key to unlock the door, and it worked. Dean then picked up his 110lb brother and dragged him over to the bed and opened his dresser and pulled out a red laced bra that was padded, a matching red laced thong, a cream short sleeved tunic dress with a black belt, and finally red platform pumps. Dean had bought brownish extensions that were very inexpensive, they matched Sam's hair almost perfectly and Sam already had bangs so he'd look even cuter.

Sam was a little curvy so the belt would help enhance that along with the bra making it look as if he had a chest.

"No," Sam said, "no, no, no and NO!" Sam repeated over and over again.

"I'm gonna get this on you one way or another so don't fight it."

"No," Sam yelled this time.

"You must be a screamer in bed," Dean mumbled with a chuckle. "Well let's get you washed up." Dean dragged Sam into the bathroom and made him get on his knees while he applied to extensions to his brother's hair. It looked pretty good and when they were done Dean told Sam to lean over the bathtub while he washed Sam's hair. Once that was done Dean dried it with a hair dryer and made him look more like a girl. He then straightened the long hair (the stolen straightener) and then that was done.

After that he told Sam to brush his teeth which he did and then he walked back into the bedroom and kneeled aggravated again. Dean applied a purple eye liner that made his younger brother's eyes pop, he then coated his eyelids a light purple and then added mascara that added 9x volume to his younger brother's already long lashes. He finally added freckles to his brother's face and a dark beauty mark under his left eye. "Sexy," Dean breathed at his feminine looking brother.

"No way," Sam said disbelievingly. "I can't look like a girl." He got up and ran to the mirror and screamed. "I do!"

"Yes you do Sylvia…that will be your name." Sam nodded in defeat and touched his face that was coated with a thick layer of make-up. "Alright, next is your outfit."

"Okay," Sam sighed, he was already this far.

"Strip off your clothes. And everything." Sam undid his shirt and jeans and slipped them off, and then hesitantly slipped off his boxers. "Arms up," Sam obeyed. "You are like a hairless rodent; you have no hair anywhere, not even pubic hair!" Sam blushed and put his arms down and attempted to cover his crotch. But Dean caught him, "Chill out, kiddo, I'll do what I have to, I'm your brother don't be nervous. It's not as if I haven't seen any of that before. Stay naked, I'll be right back." Sam blushed darker.

Dean left and came back. He was dressed in black non-ripped jeans and a navy button-down shirt that was showing a grey wife beater and he wore a dark brown jacket on top.

"Okay," Dean said and picked up the red bra, "Slip your arms through the loops, and I'll do that back." Sam slipped his arms through the loops and did the hook in the back and tightened the straps until it was perfect. "Okay put on the thong." Luckily, it was slightly padded so it looked like a female part instead of a male part. Dean gave him a once over and smiled. He then slipped the dress over his brother's torso and buckled the belt in the front. Sam slipped on the high heels and was complete.

**Step Three: Outfit and Girl. **_**Complete**_**.**

Sam looked in the mirror and didn't recognize himself.

"No way," he said for the second time today, "this can't be me."

"It is, baby brother," Dean said, "alright and now you have to act like one. Okay?"

"Okay…"

"When you walk: you have to sway your hips back and forth like so," Dean got up and awkwardly walked with his hips swaying. "You try."

"Like this," Sam asked and got up and started to walk swinging his hips back and forth and shaking his ass a little.

"Perfect," Dean said catching his breath and then quickly coughed. "You have to have a girly voice, your normal one should be fine, you don't need to talk much, just a little and adjust as you need to."

"Okay," Sam said through gritted teeth and waited for more. _Jerk_, Sam thought, _my voice isn't girly_.

"Alright I'll also always be with you, if you need to go to the bathroom, tell me and I'll go with you. Also I'll be making moves on you. Grabbing you breasts or touching your ass, just act normally okay. Want to test one out so you know what to do?"

"Okay," Sam said and shifted uneasily on his heels. Dean sat down and patted his lap.

"I want you to straddle me," Sam nodded and got on Dean's lap with his knees on either side of Dean. "You can either have your hands on my chest or around my neck," he settled with the chest. "And finally I'll be touching your legs." Sam gulped and gripped Dean's shirt tightly. Dean's hand skimmed up Sam's leg and squeezed his thigh a little making Sam just a little. Dean leaned in and bit Sam's neck softly as his fingers worked their way up the back of Sam's leg and onto his ass where he slipped his finger between the thong strap.

Sam's face was a bright red.

"And that's that," Dean smiled and Sam got off of him and then they made their way to the Impala and drove to the party.

When they arrived they were greeted by Dean's friend Tom.

"Dean," Tom smiled and then looked at Sam, "and who's this beauty?"

"Hey Tommy, this is Sylvia," Dean introduced.

"Well HEEELLLO, Sylvia," Tom winked.

"Hi," Sam squeaked and then Dean wrapped his arm around his waist.

"She's mine, Tom, no touching."

"Aww," he sighed and followed Dean as they walked in. Dean got many smiles from the girls at the party. They were all wearing slutty clothes. Sam was kind of covered.

Dean found his way to a couch where people were just lounging around and talking, it was mostly talk about sex and alcohol. Dean made a note only to give Sam water and nothing else.

The thing about Dean was that he'd hooked up with most of these girls and the most he had done was make out with them and feel them up. He has only had sex a few times, but never with these chicks. He knew for sure that Sam was clean so he kept him away from all the other guys that were staring at his brother.

So Dean sat down and patted his lap. Sam followed the role and sat on his lap, placing his hands on his chest and laying his head on Dean's shoulder and closed his eyes.

"Is she alright," a girl asked Dean when she noticed that Sam looked uneasy.

"Sylvia had a long night," Dean winked and everyone chuckled.

"She's a quiet little thing, isn't she," a boy asked.

"Just right now, she's not in bed," Dean smirked and received a high five. Sam shifted getting more comfortable and his ass was sticking in the air a little. Dean's hand shifted to his leg and rubbed it up and down. He then ran his fingers over Sam's right butt-cheek and stuck a few fingers under the thong strap like he had before, but to Sam something seemed different.

"De…?" Sam gasped and tensed up a bit.

"Relax," Dean smirked.

"I want to leave," Sam said about to cry. Dean figured that he did something wrong, he took advantage of his brother. Sam got off his lap and stalked away.

"Sylvia," one of the girls called, but Sam didn't look back.

"I should go get her," Dean said, "thanks for the invite, Tom."

"Sure thing, she's quite a catch I wouldn't want to lose her either."

"Thanks," Dean smiled, he knew it was the truth, and walked out of the party where Sam was sitting on the hood of the car with his arms to his chest and his thong showing the tiniest bit.

Sam was crying, his make-up was clearly running and he looked broken.

"Sam," Dean said wanting to cry just as much. "I'm so-"

"Just take me home." He jumped off the top of the car with his shoes in hand, he threw them in the back of the car when he got inside and leaned his head against the window still crying, but wanting to stay far away from his older brother.

When they were back in the motel room, Dean helped him get out of those clothes and unhooked the bra and left it forgotten on the floor. Sam was sobbing quietly still; he slipped out of the thong and didn't replace them with boxers he just put on a pair of Dean's grey sweats and a loose black long sleeved shirt of Dean's.

He met Dean in the bathroom. Sam sat on the edge of the bathtub and dean turned on the tub nozzle to a warm setting. He grabbed a wash cloth and then he wet Sam's hair lightly with water and then a special extension remover cream and then gently tugged at the long hair until it fell in chucks off of his head. He disposed of the long hairs in the trash can and silently soaked the washcloth under the streaming water. He opened the box where he'd gotten the make-up and took out the remover. He rubbed the make-up remover over his brother's eyes and face to make sure that it was all gone. Sam was still crying and now he had black circles under his eyes from the make-up that was too stubborn to come off.

"Do you like the taste of regret," Sam asked through tears.

"I'm so sorry Sam-"

"Do you?" Dean never knew his brother to act this way. But it was really the first time he'd REALLY pissed him off. And Sam was very persistent to get an answer, he believed that's the least that Dean could owe him, to admit that he was wrong.

"I don't, Sam, I'm so sorry I put you through that."

"I know," Sam sighed.

"I never meant for you to cry," Dean looked sad too and dabbed Sam's face with warm water and then turned off the nozzle.

"I know…"

"You do," Dean asked confused and looked into his brother's eyes. Sam nodded and then stood up and headed for the bed. He sat down slowly and Dean walked over and kneeled down in front of him, he was about Sam's height because the bed was very close to the ground.

Dean put his hand on Sam's cheek.

"I can't believe I acted like such a douche bag back there. I just wanted to impress them." Dean confessed

"I know…" Dean grew silent and Sam closed his eyes, tears still trickling out. Dean brushed away the tears from his face and leaned forward to kiss his younger brother on the face. Sam caught by surprise turned to look at his brother and ghosted Dean's lips. They both turned red and tensed, which then slowly turned into relaxation.

And then he placed a small kiss on his younger brother's forehead.

"I love you, Sammy."

"I love you too, De."

* * *

R&R that would be great!


End file.
